Acid salt of phenyl-glycocol-ortho-carboxylic acid and process of making same.



' UNITED STATES PATENT OFFICE.

PAUL SEI DEL, OF LUDWIGSHAFEN, GERMANY, ASSIGNOR TO BADISCHEI ANILIN &SODA FABRIK, OF LUDWIGSHAFEN, BAVARIA, GERMANY,

A CORPORATION OF BADEN.

ACID SALT OF PHENYL-GLYCOCOL-ORTHO-CARBOXYUC ACID AND PROCESS OF MAKINGSAME.

SPECIFICATION forming part of Letters Patent No. 690,325, datedDecembersl, 1901.

Application filed May 27, 1901. Serial No. 62,126. (No specimens.)

To all whom it may concern.-

Be it known that I, PAUL SEIDEL, doctor of philosophy and chemist, asubject of the King of Saxony, residing at Ludwigshafen-on-the- Rhine,in the Kingdom of Bavaria, Germany,

have invented new and useful Improvements in Processes for theProduction of Phenyl- Glycocol-Ortho-Carboxylic Acid and Acid SaltsThereof, of which the following is a specification.

My invention relates to a process for producingphenyl-glycocol-ortho-carboxylic acid. The processes hitherto known forthe production of this body all present drawbacks. Thus if anthranilicacid be treated in aqueous solution with chlor-acetic acid and an excessof carbonate of soda considerable quantities of an acid which may betermed anthranilo-di-acetic acid are formed andat the same time aconsiderable portion of the anthranilic acid used remains unchanged, andif anthranilic acid and mono-chlor-acetic acid be heated together inaqueous solution in a vessel provided with an inverted condenser thehydrochloric acid produced is liable to cause a decomposition of theproduct desired, and so the yield suffers, and if in this process somecarbonate of soda be added in order to neutralize the hydrochloric acidformed (see Heumann, Berichte, Vol. 23, page 3432) some decompositiontakes place.

The process,according to my invention,consists in bringing theanthranilic acid and chlor-acetic acid into reaction with one another inaqueous solution in the form of their neutral salts, or a sufficientquantity of a suitable base can be added to the solution ofequimolecular proportions of the acids, so as to neutralize them. The advantages of my process are that the reaction proceeds smoothly at a lowtemperature, so that a decomposition of thephenyl-glycocol-ortho-carboxylic acid formed is avoided. On the otherhand, owing to the formation of hydrochloric acid during the reaction anew acid salt of phenyl-glyco col-ortho-carboxylic acid is obtained, andthis is almost entirely insoluble in cold water and only slightlysoluble in moderately-warm water, so that as it forms it separatesalmost completely from the solution. and is consequently removed fromany further reaction with the chlor-acetic acid, so that theformadegrees centigradea rapid reaction sets in,

which, however, gradually proceeds more slowly. The new acid salt of thephenyl-glycocol-ortho-carboxylic acid soon begins to separate out. Itcan be collected and the mother-liquor again warmed or allowed to standfor a long time, if desired, after being enriched by the addition of afurther quantity of the alkaline salts of anthranilic acid andchlor-acetic acid and in this way a further quantity of the desiredproduct obtained.

The following example will serve to further illustrate the nature of myinvention and the manner in which the same may be carried into practicaleffect; but the invention is not confined to the reactions exemplified.The parts are by Weight.

Example: Prepare the neutral sodium salt of anthranilic acid by stirringabout one hundred and thirty-seven (137) parts of anthranilic acid to apaste with thirty (30) parts of water and neutralizing the acid by theaddition of about one hundred and twenty (120) parts of caustic-sodalye, (containing about thirty-five per cent. of NaOH.) Add to thissolution at a low temperature one hundred and sixteen (116) parts ofsodium 'chlor-acetate dissolved in two hundred (200) parts of water.farm the mixture to about forty (40) degrees centigrade and maintainthis temperature for several days. Collect the acid salt which separatesout by centrifugal action. Instead of sodium salt potash or ammoniasalts or the salts of the alkaline earths can be employed.

The chemical composition of my new salt can be expressed by the formula:

where R represents one equivalent of an alkaline metal, such as sodiumor ammonium, or half an equivalent of a metal of the alkalineearths,s"uch as barium. It is exceedingly difficultly soluble in coldwater and but slightly soluble in Water heated to forty (40) degreescentigrade. It can be obtained by crystallization from warm water inalmost-colorless crystals.

The sodium salt which I Wish to claim specifically can be represented bythe formula:

COOH O H N COONa. It is solublein water at twenty-three (23) degreescentigrade to the extent of about one and a half (1%) per cent. It canbe obtained by crystallization from warm water in almoststantially asdescribed.

which is exceedingly difficultly soluble in cold water and but slightlysoluble in Warm water, which can be obtained by crystallization fromwater in almost-colorless crystals, sub- 3. As a new body the acidsodium salt of phenyl-glycocol-ortho-carboxylic acid .whose chemicalcomposition can be expressed by the formula degrees centigrade to theextent of about one and a half (1%) per cent. and which can be obtainedby crystallization from warm water in almost-colorless crystals,substantially as described.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witnesses.

\ PAUL SEIDEL.

Witnesses:

JOHN L. HEINKE, I PERCY J. JONES.

